The “Naked” Truth About Building Trust in Sales

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What We Learned About How to Get Out of the “I Need More Details” Death Spiral Without Making Stuff Up in Your Sales Proposals.

Author: Chuck Ingram

What We Learned

Even if you are not a Chief Revenue Officer – Sales methodology and sales tech is a huge topic these days. Companies must grow; they can’t hire more people and they have bought a lot of sales techs – And none of it seems to be helping.

One especially tricky topic that comes up a lot is companies, and their potential buyers are getting stuck in seemingly endless iterations around sales proposals.  It can often feel like a high-stakes game of whack a mole, with client conversations around getting more information before making a commitment.

Just when you think you have answered a question – another one pops up. At some point – and we have all been there – the answer becomes – “we don’t know that yet” – or (please don’t do this) we will have to start making things up.

This scenario signals an underlying issue: a lack of trust and confidence. In this era of all thing’s digital disruption and AI, it seems perhaps unpopular but nonetheless important to revisit the human element in business relationships and better conversations to reinvigorate this trust.

I would highly recommend reading (or rereading) Patrick Lencioni’s still relevant book, “Getting Naked: A Business Fable About Shedding The Three Fears That Sabotage Client Loyalty.”

There are a few principles in this book that at our firm – congruentX we have learned seem super relevant that I thought I would share – especially these days.

“Give Away the Business”

No matter what your business is – there is always the delicate balance of showing your client that you can help them – but at the same time – getting paid for your product or service.

Inspired by a conversation by the always super insightful Candyce Edelyn – I went back and looked at quite a few of the best relationships we have today with clients. Then I thought about how we started working together. Since we record, transcribe, and summarize every call with DialoguePrime for Viva Sales – it wasn’t too hard to do????.

Looking at those clients – they seemed to mostly start the same way – No introduction deck.  No deck on our unique methodology or our offerings. Sometimes we did send an “about us” one pager beforehand.

We just literally asked questions and started helping. It turned into a business relationship.

Don’t be Afraid of Losing the Business

Early on in our business we were afraid of losing any potential opportunity. We are a CRM firm. Most people realize that companies are only happy with their CRM implementations about half the time. Success is a flip of the coin.

There are some absolute go dos if you want to “Get CRM Right”. At the same time there are some things we have learned over hundreds of implementations – that are a recipe for failure.

We realized that when we made honest recommendations to our potential clients. Whether it was not doing a big bang project, not bringing the business IT and users together or designing for user context not building big forms in the name of a 360-degree view.

Many of our happiest clients had another firm make all the mistakes I described in the paragraph above. And in some cases, somebody with the absolute best intentions on the client’s side was demanding as much.

By sharing the “Kind truth” – We might lose the business. And that’s ok.

Ask “Dumb Questions” and “Make Dumb Suggestions”

There’s a lot about challenger selling, that’s right.   There are also parts of challenger selling that when executed the wrong way can instead of building credibility by teaching can create difficult missed opportunities.

Mike Hauck, one of my business partners is a fantastic question asker. Sometimes he will frame a question as a “dumb” question. I’ve seen (lots) more than one time – a “dumb” question even one that exposes potential vulnerability, or lack of industry knowledge, will uncover an insight that was while not in the client’s requirements document – unique to a client’s business and pays the client back 10x in return on investment.


In conclusion, building trust in sales transcends a methodology or digital playbook —it involves embracing the human elements of vulnerability, honesty, and genuine curiosity. Our client conversations at congruentX, informed by the wisdom of Patrick Lencioni’s “Getting Naked,” (plus goofing up often) remind us that sometimes, the best way to avoid the “I Need More Details” death spiral is to prioritize the client’s needs above the immediate prospect of a sale.

By showing a willingness to lose the business, by freely offering value, and by unashamedly asking ‘dumb’ questions, we can uncover unique insights that deliver outstanding ROI and foster lasting business relationships. As we navigate an increasingly digital marketplace, these principles serve as an important reminder of the power of trust and authentic human connection in driving successful sales.

If you want to learn more about this topic – please check out Patrick’s book. If you want to learn more details about how to have those amazing business conversations at scale – Please read “Speaking Frankly about Conversation Intelligence” by JC Quintana.

Finally – If you are pumped up and want to talk now about how to drive shorter sales cycle times, close rates and customer lifetime value by having better sales conversations – please schedule some time with JC and me here.   We will even send you JCs book in advance just to get prepped!

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